


Sheriff Stilinski's Guide to Courting

by whenshewrites



Series: A Collection of One-Shots and Tumblr Prompts [48]
Category: Teen Wolf (TV)
Genre: Awesome Sheriff Stilinski, Dating Attempts, Derek Hale Deserves Nice Things, Derek Hale Loves Stiles Stilinski, Derek Hale is Not Emotionally Constipated, Derek Hale is Not a Failwolf, Fluff, Humor, Idiots in Love, M/M, One Shot, Originally Posted on Tumblr, Protective Sheriff Stilinski, Sheriff Stilinski Feels, Sheriff Stilinski Ships It, Sheriff Stilinski's Name is John, Stiles Stilinski is a Little Shit, Stiles Stilinski is a Tease, The Hale Pack - Freeform, Werewolf Courting, except not really
Language: English
Status: Completed
Published: 2020-07-05
Updated: 2020-07-05
Packaged: 2021-03-04 23:35:27
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,291
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25084750
Author URL: https://archiveofourown.org/users/whenshewrites/pseuds/whenshewrites
Summary: John would rather not actively participate in his son’s love life, thank you very much. But he was pretty sure he didn't have a choice.
Relationships: Derek Hale/Stiles Stilinski
Series: A Collection of One-Shots and Tumblr Prompts [48]
Series URL: https://archiveofourown.org/series/1956889
Comments: 30
Kudos: 648





	Sheriff Stilinski's Guide to Courting

**Author's Note:**

  * For [3White_Mage3](https://archiveofourown.org/users/3White_Mage3/gifts).



John was pretty sure this shouldn’t be his problem.

He would rather not actively participate in his son’s love life, thank you very much. Especially when he was pretty sure his son’s ‘love life’ consisted of chaotic pining after the angry werewolf that the Sheriff had been working to put behind bars two years ago. 

See, John was pretty sure said angry werewolf might be pining after his son too. Just not as chaotically. In fact, there was no chaos. Just longing looks and angsty glares that made even John want to groan.

He was pretty sure this wasn’t his problem. His time should never be spent actively participating in his son’s love life.

But then the Sheriff realized the only way he was ever getting any mental peace again would be when his son and Derek Hale were no longer dancing around each other. And so, with a sinking heart, the Sheriff realized he was going to have to take part in making sure that happened.

First of all, he would like to say he did not ask for this. 

Second of all, it was hard.

It started when John walked past his son’s room one day, paused, and then quickly backtracked to see Derek sitting on his son’s bed.

Stiles was nowhere to be seen. The kid was still at lacrosse practice if John remembered right, and probably wouldn’t be home for another hour or so. But here Derek was, sitting. On Stiles’s bed. Alone in an empty room with his leather jacket sitting on his lap and his face always perpetually scowling. Until he saw the Sheriff staring, that was.

John blinked at him and Derek blinked back. The man had gone shock-still, looking like a deer caught in headlights, and his eyes were full-blown wide. Leaning against the bedroom door, John raised one eyebrow and sighed.

“Hello there, Derek.”

“Sir.”

“Do I want to ask what you’re doing here?”

The man shifted uncomfortably. “I’m waiting for Stiles.”

“He’s at the school.”

“I know.”

“And he won’t be back for a while still.”

“... I know.”

The Sheriff pressed his lips together and nodded. He really didn’t think he wanted to press, but he was pretty sure he couldn’t leave Derek sitting alone in his son’s bedroom either. Because that would be wrong, right? That would probably be wrong.

“Might I ask why you’re waiting for Stiles?”

For a long moment, he didn’t get an answer. Then Derek ducked his head and mumbled the word “Research” so quietly, John almost didn’t catch it. Because unlike Hale, he wasn’t a werewolf. He didn’t have super hearing, dammit. 

John made a mental note not to remind himself it was a werewolf— not just a man— sitting in his son’s bedroom. Because he was pretty sure that would create a whole new list of problems.

“So, research,” he said, almost enjoying the look on Derek’s face. “That’s all?”

“Yes sir.”

“There’s nothing else going on here?”

Derek’s face turned bright red and he quickly shook his head. The Sheriff pressed his lips together and nodded. There were a lot more things he could say; a lot more things he should probably say. But John decided that was enough interference for the day. He’d have a conversation with Stiles when he got back from practice. 

You know, about how werewolves probably shouldn’t be camping out in his room on a school day.

“Okay then,” John said, and Derek looked both shocked and relieved. “If you want a cup of coffee while you’re waiting, the kitchen’s wide open. And if you made Stiles a snack for when he gets home, I’m pretty sure he’ll be much more receptive to this… research.”

Derek stared at him with wide eyes before nodding. John chuckled and turned away, continuing back down the hall. He thought he’d handled that fairly well. Or… as well as possible, at least. How was he even supposed to address something like that?

John was pretty sure he didn’t want to get involved. He really didn’t want to get involved.

He just didn’t realize yet that he didn’t have a choice.

-

The next time John stumbled across things he didn’t mean to, he started to realize he either went along with it or moved to another town. Because Derek Hale was always there. And it seemed his son was too.

John liked when he got to do the grocery shopping because that meant he could buy the things he wanted to. Stiles never let him buy steak or frozen meals or anything actually edible when he tagged along, and when the boy went out by himself, he never came home with anything other than vegetables and whole wheat pasta. So John cherished the days when he could do the shopping himself.

The moment he entered the store, he made a beeline for the frozen meats section. But John didn’t expect to pass the ‘Personal Care Products’ aisle and see two figures standing there that he recognized  _ very  _ well. 

Moving slowly back, John peered at Derek and his son, and then glanced at the different packages of bandages that Stiles was holding.

“These might be cheaper, Derek,” the boy said, waving one through the air. “But they also sop up less blood. When one of us is bleeding out, Sourwolf, which would you prefer? The bandages that last five seconds and then let you bleed to death, or the ones that basically hold you together?”

“I would rather not have either of us bleeding out at all,” Derek said flatly, and the Sheriff decided truer words had never been spoken. He’d never thought he’d be listening to his son talk about his possible injury and death, but no father should have to hear something like that. Ever.

He stepped forward, clearing his throat, and both Stiles and Derek whirled around.

Derek’s eyes went as wide as saucers. But Stiles only went shock-still for a moment before putting a bright smile on his face and straightening up.

“Pops, dad, father-mine! What a coincidence to see you here!”

“Coincidence indeed,” the Sheriff said, looking at the bandages and then back at his son. “Can I assume someone is not currently dying?”

“Not yet!”

“Not… yet.”

“Stiles,” Derek hissed, elbowing the boy in the ribs. Stiles made a protesting noise of pain and elbowed the man back, and the Sheriff resisted the urge to facepalm.

This was his son, ladies and gentleman. And the Alpha werewolf he had somehow come to tame.

“So,” John said. “This is what you do in your free time?”

“Only when necessary.”

“Do I want to know what that means?”

Stiles ran a hand through his hair and shrugged, a sheepish look replacing the one of amusement on his face. “Only when we run  _ out  _ of bandages.”

The meaning behind that was obvious. John really questioned everything sometimes; like maybe his decision to not lock Stiles in his room and make him study online until graduation. Then he could let him back out into the world and make sure he went to college somewhere far, far away from Beacon Hills.

The Sheriff really lingered on that fantasy sometimes. Even though he knew he’d never be able to tear Stiles away from the supernatural. Not today, not tomorrow. He hoped maybe one day the boy would finally get some peace, but that didn’t seem to be in the near future.

Derek’s face was scarily pale beside the boy. John only sighed.

“You’re going to be the death of me.”

“I will not,” Stiles said, dropping the more expensive bandages into the basket that Derek held and moving forward to snoop through the Sheriff’s cart. He wrinkled his nose and picked out a bag of chips, a container of cookies, and a loaf of white bread that the Sheriff had put in there earlier. “But these will. This is why you’re not allowed to go grocery shopping alone.”

“It warms my heart when my son tells me what to do.”

“Only because I care,” Stiles said with a grin, putting the items in Derek’s basket instead of back in the Sheriff’s cart. John was sad to see the cookies go. “Now you may go check out, pops. And don’t even think about making a pit stop in the frozen meats section.”

“I deserve steak,” the Sheriff mumbled. Stiles snorted.

“You deserve to live a nice long, full life without any heart problems.”

“You’re a heart problem.”

“See,” Stiles said, glancing toward Derek. “You think you have it rough dealing with me. When my dad gets hungry, he’s like a pouty teenager. Even though we all know he’s much too old to ever be considered a teenager again.”

“Okay,” the Sheriff said, grabbing his cart and starting past them. “And now I’ve had enough of my own son for the day.”

“I love you, pops!”

John only huffed. But before he moved fully by, he hesitated and grabbed a bottle of hydrogen peroxide, setting it in the basket next to the bandages. Derek’s face did fifty more things, finally resting on blank terror, and the Sheriff was quietly pleased that he could incur such fear in a man like Derek Hale.

Because Derek Hale was a werewolf. John was pretty sure that when he was shifted, even a bullet to the chest would take its time stopping him.

But clearly John’s mere presence made Derek tremble in his fancy leather jacket. 

“Quick tip,” John said quietly, leaning closer so Stiles couldn’t hear. “If you buy him a packet of Reeses at checkout, he’ll be well behaved for the rest of the day.”

Derek’s eyes snapped to the Sheriff’s face and he just stared for a moment. Then, still pale, Derek nodded. The Sheriff smiled and moved back away. He didn’t glance back, but he could feel Derek watching at him the entire time he moved down the aisle.

John didn’t buy himself any steak, mourning that loss. But he did pick up a packet of Reeses for his own self at checkout. Because he was a simple man and chocolate was therapy.

And John had no doubts he was going to need a lot of chocolate before this was all over.

\- -

See, the Sheriff didn’t know why he was going along with all of this. He was pretty sure it would make his life easier in the end but with a son like Stiles, he couldn’t know that for sure. 

It just seemed once the Sheriff started stumbling across things, apparently he couldn’t stop.

He tried to sneak into the diner and found Stiles laughing in a booth with Derek at his side. The man had looked like he was about to pass out when Stiles had gone to the bathroom and John had crossed over, offering a wide smile and pointing out that Stiles liked milkshakes, so Derek should attempt that.

Not a week later, Derek was arrested for standing outside the Stilinski house at night (not by John, of course. He’d gotten used to Hale and his strange habits by now) and the Sheriff had been the one to let him off, saying maybe he should consider talking to Stiles instead of silently lingering in the shadows.

One month passed and the Sheriff realized he was criss crossing paths with Derek and his son everywhere. At the movies (‘pack night’ without the pack), out in the preserve (‘stakeout’), and back in Stiles’s bedroom for a second time (except it was 2 am and Stiles was there too. John would believe ‘research’ when pigs started to fly). 

And the thing was John was pretty sure this shouldn’t be his problem.

He hadn’t asked to be caught in the middle of his son chaotically pining after Derek Hale and Derek Hale aggressively but silently pining back. Nothing John had ever experienced had prepared him for this.

And in the end, he realized it came down to him. John didn’t think that was fair at all.

To his surprise though, he didn’t have to make the first move. John didn’t expect to hear his doorbell go off that day and he really didn’t expect to see Derek Hale on the other side when he opened the door. Because Hale never rang the doorbell. In fact, John had always thought he didn’t even know that was a thing.

Derek shifted from foot to foot with his hands stuffed in his pockets. John raised a brow.

“Good afternoon, Derek.”

“Sir.”

“Stiles isn’t here.”

It was so similar to their first conversation, the Sheriff didn’t know why they hadn’t just had it months ago. Derek’s face turned bright red and he ducked his head, nodding. “I know.”

“So is there anything I can help you with?”

If possible, Derek’s face turned even brighter red. He looked at the ground for a moment before raising his eyes. “I came here to talk to you, sir.”

“You don’t have to call me sir, Derek.”

“... Sheriff?”

“John is fine, son.”

John didn’t know what he was expecting, but for Derek to look shocked and then terrified wasn’t it. For a moment, he truly thought the man would make a run for it. But then Derek cleared his throat and nodded, and John stepped aside, opening the door wider.

Derek stepped inside, glancing around. He shuffled his feet and John was pretty sure he had never seen the man look so nervous.

“So, Derek. You came to speak to me?”

“I don’t know what you’re doing, sir.”

The Sheriff blinked at him. That also wasn’t what he was expecting. “Sorry?”

“Stiles is… always around lately, sir,” Derek said quietly. “And I like him being around. But I’m… not good with that. Until you’ve helped me be good with that. But I don’t know why you’re helping me be good with that.”

Oh.  _ Oh. _

“I’m sorry,” Derek said quietly. “I can go and make sure he doesn’t come back to the loft again. I didn’t mean to—”

“Derek, what the hell are you talking about?”

Derek looked up and his expression could only be described as shocked confusion. The man glanced around the room, toward the door, and then back at John. “If you don’t want me around him. If that’s not what you meant to do. I can make sure it doesn’t happen again—”

“You will do no such thing.”

Derek’s mouth snapped closed and he just looked surprised. The Sheriff rubbed a hand over his face, sighing. “Derek, you like my son, don’t you?”

“... Sir.”

“Stop calling me that.”

“Sheriff.”

“Derek.”

“John,” the man said quietly. “I’m sorry.”

“Please stop apologizing.”

Derek looked like that’s the last thing he had been expecting. John resisted the urge to go to the kitchen and grab a beer. He thought he deserved one, but he didn’t think Derek deserved the terror that would probably follow such actions. So instead, he gestured to the couch and, as Derek slowly moved over and sat down, sank into the armchair opposite of him.

“The last thing I want for you to do is push Stiles away,” John said. Derek’s eyebrows shot up and John waved a hand through the air. “Don’t get me wrong, I wasn’t excited about it at first. But he’s… happy. More than he has been in a while.”

Derek didn’t move. Didn’t say a word. John studied his face.

“Will you ever hurt my son, Derek?”

“Of course not.”

“Will you ever put him in danger or put yourself before him?”

“Never.”

“Then I don’t know what you want me to say, son,” the Sheriff said, tilting his head. “Do you want me to tell you not to see my son anymore?”

Derek actually looked like he was considering that for a moment. And suddenly, all John could see was the fifteen-year-old kid sitting in the Sheriff’s station, wrapped in a blanket, covered in ash, and staring blankly at the floor. The very image hurt him.

Finally, Derek shook his head. “No, sir.”

“John.”

“No… John.”

“Then let me get you a drink,” John said, pushing himself up and moving toward the kitchen. He stayed in there longer than was probably necessary, but he was still trying to figure out the man currently sitting on his couch. Derek Hale was… well, he was something.

When the Sheriff came back out, Derek looked like he’d been sitting stock-still the entire time. John passed him a beer and sighed.

“So what do you need?”

“Si— John?”

“What is it called when a werewolf courts a human, Derek? Do I even want to know?”

Derek’s face turned bright red. “It’s just dating, sir.”

“And are you planning on doing that?”

Derek stared at him; silent and blank faced. John sighed for what felt like the hundredth time, rubbing a hand over his face.

“Are you planning on dating my son, Derek?”

He might as well have threatened to shoot the man. Derek tensed up and glanced toward the door and once more, the Sheriff wondered if he’d genuinely make a run for it. He quickly raised his hands like he was trying to calm a startled animal.

“I asked the question, Derek, I’m not going to shoot you for answering.”

“I… I don’t know, sir. Sheriff. John.”

“Are you wanting to?”

Derek glared at his beer as if it had personally offended him. But he still nodded. The Sheriff wondered for a moment how he’d gotten into this position before remembering he’d basically let Hale into his house in the first place. Technically, this was his fault.

“Just get him curly fries before you ask, Derek. Curly fries put Stiles in a state of euphoria.”

Derek’s eyes snapped up. “What?”

“Curly fries, Derek.”

“You’re giving me permission to date your son?”

“If you hurt him in any way,” the Sheriff said, pointing a finger at the man. “I will personally stock up on wolfsbane bullets and make good use of them.”

Derek’s face whitened. He nodded silently.

“You’re a good kid, Derek,” John said, dropping his hand. “I don’t expect that’ll ever be necessary.”

“No, sir.”

“Though it might be if you continue calling me sir.”

“No, John.”

The Sheriff smiled at that. This was progress, he thought. Not that he’d ever seen himself giving ex fugitive and literal werewolf Derek Hale advice on how to court his son. He wondered if Claudia would be exasperated or proud of him.

Probably both.

“So,” the Sheriff said. “Anything else?”

Derek glanced from his bottle, to the Sheriff, and then toward the door. Shaking his head, he pushed himself up and set the bottle on the coffee table. He hadn’t even touched it. “No, John. Uh… thank you.”

“Please never mention this to Stiles.”

John could’ve sworn Derek nearly smiled. He hadn’t thought that was possible (did it come with being a werewolf or was that an eyebrow thing?) but John was pretty sure he knew what he saw. Derek Hale smiling. In his house. What a trip.

This entire visit was unexpected from one point to the next. 

The Sheriff followed him to the door and Derek looked like he was going to say something else, but then he turned and quickly exited the house. John watched him all the way to his Camaro before shutting the door with a long, heavy sigh.

He would like to say first of all, he did not ask for this. 

Second of all, it was hard _. _

And third of all? Well, the Sheriff needed some chocolate. Maybe a few steaks. But he also thought that could have been worse; and he was never doing it again.

His time should never be spent actively participating in his son’s love life.

Never again. 

**Author's Note:**

> Based on the prompt 'John attempting to give Derek dating advice' and this was so much fun to write. Of course, I'd love to hear what you guys thought! I hope you're all doing well <3
> 
> Come hang with me on Tumblr?
> 
> [the dumpster](https://when-she-writes-stuff.tumblr.com/)


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